#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008972.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2008972
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  1486
_journal_page_last  1489
_publ_section_title
;
Four interpenetrating three-dimensional frameworks in the
hydrogen-bonded structure of
5-hydroxyisophthalic acid--4,4'-trimethylenedipyridine (1/1)
;
loop_
_publ_author_name
  'Wheatley, Paul S.'
  'Lough, Alan J.'
  'Ferguson, George'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C13 H15 N2 + , C8 H5 O5 -'
_chemical_formula_sum  'C21 H20 N2 O5'
_chemical_formula_weight  380.39
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x, -y+1/2, z+1/2'
  '-x, -y, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  19.2490(6)
_cell_length_b  7.3915(4)
_cell_length_c  12.6587(6)
_cell_angle_alpha  90.00
_cell_angle_beta  92.554(3)
_cell_angle_gamma  90.00
_cell_volume  1799.28(14)
_cell_formula_units_Z  4
_cell_measurement_temperature  100.00(10)
_exptl_crystal_density_diffrn  1.404
_diffrn_ambient_temperature  100.00(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  O11 0.16397(6) 0.10457(18) 0.54124(9) 0.0281(3) Uani d . 1 . . O
  O12 0.10422(5) 0.11595(18) 0.38526(9) 0.0256(3) Uani d . 1 . . O
  O21 0.45290(5) -0.2155(2) 0.41673(9) 0.0319(3) Uani d . 1 . . O
  O22 0.39062(5) -0.23566(17) 0.56013(8) 0.0227(3) Uani d . 1 . . O
  O5 0.27376(6) -0.09049(18) 0.12163(8) 0.0259(3) Uani d . 1 . . O
  C1 0.21964(7) 0.0026(2) 0.38821(12) 0.0191(4) Uani d . 1 . . C
  C2 0.27752(8) -0.0556(2) 0.44901(12) 0.0194(4) Uani d . 1 . . C
  C3 0.33494(7) -0.1257(2) 0.39947(12) 0.0188(4) Uani d . 1 . . C
  C4 0.33453(8) -0.1334(2) 0.29013(12) 0.0189(4) Uani d . 1 . . C
  C5 0.27642(8) -0.0784(2) 0.22901(12) 0.0200(4) Uani d . 1 . . C
  C6 0.21853(8) -0.0101(2) 0.27886(13) 0.0204(4) Uani d . 1 . . C
  C11 0.15974(8) 0.0793(2) 0.44597(13) 0.0205(4) Uani d . 1 . . C
  C21 0.39767(8) -0.1966(2) 0.46260(12) 0.0207(4) Uani d . 1 . . C
  N31 0.00701(7) 0.2461(2) 0.50221(11) 0.0237(3) Uani d . 1 . . N
  C32 0.02280(8) 0.2900(3) 0.60319(13) 0.0259(4) Uani d . 1 . . C
  C33 -0.02491(8) 0.3608(3) 0.66974(13) 0.0242(4) Uani d . 1 . . C
  C34 -0.09362(8) 0.3882(2) 0.63301(12) 0.0204(4) Uani d . 1 . . C
  C35 -0.10933(8) 0.3444(3) 0.52836(13) 0.0233(4) Uani d . 1 . . C
  C36 -0.05848(8) 0.2744(3) 0.46678(13) 0.0255(4) Uani d . 1 . . C
  N41 -0.47424(6) 0.6845(2) 0.62217(11) 0.0237(3) Uani d . 1 . . N
  C42 -0.42377(8) 0.6751(3) 0.55319(13) 0.0243(4) Uani d . 1 . . C
  C43 -0.35654(8) 0.6349(2) 0.58748(13) 0.0223(4) Uani d . 1 . . C
  C44 -0.34061(8) 0.6047(2) 0.69398(12) 0.0190(4) Uani d . 1 . . C
  C45 -0.39527(8) 0.6139(3) 0.76269(13) 0.0261(4) Uani d . 1 . . C
  C46 -0.46143(8) 0.6549(3) 0.72541(13) 0.0276(4) Uani d . 1 . . C
  C51 -0.14622(7) 0.4602(3) 0.70695(13) 0.0227(4) Uani d . 1 . . C
  C52 -0.21736(7) 0.5040(2) 0.65538(12) 0.0204(4) Uani d . 1 . . C
  C53 -0.26853(7) 0.5610(2) 0.73737(12) 0.0202(4) Uani d . 1 . . C
  H12 0.0721 0.1521 0.4228 0.038 Uiso calc R 1 . . H
  H5 0.3105 -0.1387 0.1017 0.039 Uiso calc R 1 . . H
  H2 0.2779 -0.0475 0.5239 0.023 Uiso calc R 1 . . H
  H4 0.3744 -0.1766 0.2564 0.023 Uiso calc R 1 . . H
  H6 0.1786 0.0274 0.2379 0.025 Uiso calc R 1 . . H
  H32 0.0691 0.2714 0.6301 0.031 Uiso calc R 1 . . H
  H33 -0.0111 0.3909 0.7406 0.029 Uiso calc R 1 . . H
  H35 -0.1551 0.3625 0.4990 0.028 Uiso calc R 1 . . H
  H36 -0.0707 0.2446 0.3953 0.031 Uiso calc R 1 . . H
  H41 -0.5169 0.7108 0.5991 0.028 Uiso calc R 1 . . H
  H42 -0.4343 0.6963 0.4802 0.029 Uiso calc R 1 . . H
  H43 -0.3210 0.6279 0.5380 0.027 Uiso calc R 1 . . H
  H45 -0.3866 0.5914 0.8360 0.031 Uiso calc R 1 . . H
  H46 -0.4981 0.6623 0.7730 0.033 Uiso calc R 1 . . H
  H51A -0.1272 0.5714 0.7409 0.027 Uiso calc R 1 . . H
  H51B -0.1525 0.3698 0.7635 0.027 Uiso calc R 1 . . H
  H52A -0.2125 0.6029 0.6034 0.024 Uiso calc R 1 . . H
  H52B -0.2356 0.3963 0.6169 0.024 Uiso calc R 1 . . H
  H53A -0.2718 0.4624 0.7898 0.024 Uiso calc R 1 . . H
  H53B -0.2496 0.6687 0.7752 0.024 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O11 0.0239(6) 0.0394(9) 0.0213(7) 0.0080(5) 0.0031(5) -0.0023(6)
  O12 0.0167(6) 0.0358(8) 0.0246(6) 0.0067(5) 0.0036(5) -0.0014(6)
  O21 0.0159(6) 0.0568(10) 0.0234(6) 0.0072(5) 0.0051(5) 0.0070(6)
  O22 0.0187(5) 0.0319(8) 0.0176(6) 0.0013(5) 0.0018(4) 0.0019(5)
  O5 0.0221(6) 0.0382(9) 0.0176(6) 0.0064(5) 0.0016(4) 0.0001(5)
  C1 0.0165(7) 0.0169(9) 0.0240(9) -0.0006(6) 0.0032(6) -0.0002(7)
  C2 0.0189(7) 0.0215(10) 0.0178(8) -0.0003(6) 0.0019(6) 0.0002(7)
  C3 0.0156(8) 0.0204(9) 0.0203(8) -0.0027(6) 0.0015(6) 0.0018(7)
  C4 0.0152(7) 0.0195(9) 0.0223(8) 0.0002(6) 0.0047(6) 0.0015(7)
  C5 0.0207(8) 0.0216(10) 0.0178(8) -0.0017(7) 0.0015(6) 0.0006(7)
  C6 0.0175(8) 0.0210(10) 0.0227(9) 0.0017(6) -0.0009(6) 0.0031(7)
  C11 0.0182(8) 0.0209(10) 0.0225(9) 0.0008(6) 0.0019(6) 0.0011(7)
  C21 0.0182(8) 0.0237(10) 0.0201(8) -0.0004(7) 0.0020(6) 0.0000(7)
  N31 0.0193(7) 0.0247(9) 0.0274(8) 0.0020(6) 0.0039(6) 0.0012(7)
  C32 0.0178(8) 0.0332(12) 0.0267(9) 0.0040(7) 0.0019(7) 0.0053(8)
  C33 0.0198(8) 0.0308(11) 0.0222(9) 0.0022(7) 0.0009(7) 0.0030(8)
  C34 0.0175(8) 0.0195(10) 0.0243(9) -0.0003(6) 0.0023(6) 0.0030(7)
  C35 0.0166(8) 0.0290(11) 0.0242(9) 0.0006(7) 0.0018(6) 0.0003(7)
  C36 0.0214(8) 0.0305(12) 0.0248(9) -0.0001(7) 0.0014(7) -0.0033(8)
  N41 0.0157(6) 0.0313(9) 0.0239(8) 0.0036(6) 0.0004(5) 0.0004(6)
  C42 0.0221(8) 0.0298(11) 0.0213(9) 0.0006(7) 0.0030(7) 0.0025(8)
  C43 0.0190(8) 0.0263(10) 0.0219(9) 0.0013(7) 0.0037(6) 0.0001(7)
  C44 0.0190(8) 0.0162(9) 0.0218(9) 0.0004(6) 0.0012(6) -0.0021(7)
  C45 0.0218(8) 0.0382(12) 0.0183(9) 0.0032(7) 0.0010(7) 0.0000(8)
  C46 0.0213(8) 0.0387(12) 0.0232(9) 0.0045(7) 0.0058(7) 0.0009(8)
  C51 0.0174(8) 0.0289(11) 0.0216(9) 0.0022(7) 0.0005(6) -0.0008(7)
  C52 0.0160(8) 0.0239(10) 0.0213(9) 0.0012(6) 0.0011(6) -0.0002(7)
  C53 0.0175(7) 0.0231(10) 0.0199(8) 0.0020(6) -0.0005(6) 0.0002(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O11 C11 . 1.220(2) y
  O12 C11 . 1.317(2) y
  O21 C21 . 1.242(2) y
  O22 C21 . 1.281(2) y
  O5 C5 . 1.361(2) y
  C1 C6 . 1.387(2) no
  C1 C2 . 1.394(2) no
  C1 C11 . 1.503(2) no
  C2 C3 . 1.395(2) no
  C3 C4 . 1.385(2) no
  C3 C21 . 1.512(2) no
  C4 C5 . 1.392(2) no
  C5 C6 . 1.399(2) no
  N31 C32 . 1.341(2) y
  N31 C36 . 1.335(2) y
  C32 C33 . 1.377(2) no
  C33 C34 . 1.397(2) no
  C34 C35 . 1.384(2) no
  C34 C51 . 1.506(2) no
  C35 C36 . 1.379(2) no
  N41 C42 . 1.337(2) y
  N41 C46 . 1.337(2) y
  C42 C43 . 1.379(2) no
  C43 C44 . 1.387(2) no
  C44 C45 . 1.396(2) no
  C44 C53 . 1.505(2) no
  C45 C46 . 1.372(2) no
  C51 C52 . 1.525(2) no
  C52 C53 . 1.522(2) no